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Sold for $1,850,000
    • $1,850,000

    431 West Wakefield Boulevard, Winchester, CT 06098

    9beds
    7,000sqft
    Single Family Residence
    Built in 2002
    3 Acres Lot
    $-- Zestimate®
    $264/sqft
    $-- Estimated rent

    Home value

    Not available

    Estimated sales range

    Not available

    Not available

    Zestimate® history
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    What's special

    Waterfront estateCharming guest bungalowPrivate dockPanoramic water viewsRelax by the shorelineCustom craftsmanship throughoutGourmet finishes
    Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

    Zillow last checked:

    Listing updated:

    Listed by:

    Lisa A. Ogren (860)416-2085,

    Berkshire Hathaway NE Prop. 860-677-7321

    Bought with:

    Annie Simard, RES.0822960

    LPT Realty

    Source: Smart MLS,MLS#: 24159989MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 9
    • Bathrooms: 6
    • Full bathrooms: 5
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Bonus Room
    Primary bedroom
    • Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Walk-In Closet(s)
    • Level: Main
    • Area: 336 Square Feet
    • Dimensions: 21 x 16
    Bedroom
    • Features: Ceiling Fan(s)
    • Level: Upper
    • Area: 345 Square Feet
    • Dimensions: 23 x 15
    Bedroom
    • Features: Ceiling Fan(s)
    • Level: Upper
    • Area: 299 Square Feet
    • Dimensions: 23 x 13
    Bedroom
    • Features: Ceiling Fan(s)
    • Level: Upper
    • Area: 276 Square Feet
    • Dimensions: 23 x 12
    Bedroom
    • Features: Ceiling Fan(s)
    • Level: Upper
    • Area: 276 Square Feet
    • Dimensions: 23 x 12
    Bedroom
    • Level: Upper
    Bedroom
    • Level: Upper
    • Area: 182 Square Feet
    • Dimensions: 13 x 14
    Bedroom
    • Level: Upper
    • Area: 264 Square Feet
    • Dimensions: 24 x 11
    Bedroom
    • Level: Upper
    • Area: 288 Square Feet
    • Dimensions: 24 x 12
    Dining room
    • Features: Remodeled, Bay/Bow Window, Built-in Features, Patio/Terrace
    • Level: Main
    • Area: 208 Square Feet
    • Dimensions: 16 x 13
    Family room
    • Features: Fireplace
    • Level: Lower
    Kitchen
    • Features: Bay/Bow Window, Eating Space
    • Level: Main
    • Area: 360 Square Feet
    • Dimensions: 24 x 15
    Library
    • Level: Main
    • Area: 208 Square Feet
    • Dimensions: 16 x 13
    Living room
    • Features: Fireplace
    • Level: Main
    • Area: 1518 Square Feet
    • Dimensions: 33 x 46
    Other
    • Level: Upper
    • Area: 253 Square Feet
    • Dimensions: 23 x 11
    Heating
    • Baseboard, Oil
    Cooling
    • Attic Fan, Window Unit(s)
    Appliances
    • Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Dryer, Water Heater
    • Laundry: Lower Level
    Features
    • Central Vacuum
    • Doors: French Doors
    • Basement: Full,Heated,Garage Access,Interior Entry,Liveable Space
    • Attic: Heated,Finished,Floored
    • Number of fireplaces: 4
    Interior area
    • Total structure area: 7,000
    • Total interior livable area: 7,000 sqft
    • Finished area above ground: 5,530
    • Finished area below ground: 1,470

    Property

    Parking
    • Total spaces: 9
    • Parking features: Barn, Attached, Off Street, Driveway, Garage Door Opener, Private, Paved
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Patio & porch: Deck, Covered
    • Has view: Yes
    • View description: Water
    • Has water view: Yes
    • Water view: Water
    • Waterfront features: Waterfront, Lake, Beach, Dock or Mooring, Water Community
    Lot
    • Size: 3 Acres
    • Features: Additional Land Avail., Few Trees, Level, Landscaped, Rolling Slope
    Details
    • Additional structures: Cabana
    • Parcel number: 924886
    • Zoning: HLD

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Cape Cod,Colonial
    • Property subtype: Single Family Residence
    Materials
    • Vinyl Siding
    • Foundation: Concrete Perimeter
    • Roof: Asphalt
    Condition
    • New construction: No
    • Year built: 2002

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Well
    • Utilities for property: Cable Available

    Community & HOA

    Community
    • Features: Public Rec Facilities
    • Security: Security System
    HOA
    • Has HOA: No
    Location
    • Region: Winsted

    Financial & listing details

    • Price per square foot: $264/sqft
    • Tax assessed value: $832,720
    • Annual tax amount: $24,982
    • Date on market: 5/7/2026

    Price history

    DateEventPrice
    9/4/2026Sold$1,850,000$264/sqft
    Source: Smart MLS #24159989 Report a problem
    8/3/2026Pending sale$1,850,000$264/sqft
    Source: Smart MLS #24159989 Report a problem
    5/7/2026Listed for sale$1,850,000$264/sqft
    Source: Smart MLS #24159989 Report a problem
    4/20/2026Listing removed$1,850,000$264/sqft
    Source: Berkshire Hathaway HomeServices New England Properties #24159989 Report a problem
    3/25/2026Listed for sale$1,850,000-15.9%$264/sqft
    Source: Smart MLS #24159989 Report a problem
    2/1/2026Listing removed$2,199,000$314/sqft
    Source: Smart MLS #24042374 Report a problem
    7/9/2025Price change$2,199,000-15.4%$314/sqft
    Source: Smart MLS #24042374 Report a problem
    3/26/2025Listed for sale$2,600,000-7.1%$371/sqft
    Source: Smart MLS #24042374 Report a problem
    9/4/2024Listed for sale$2,800,000+154.5%$400/sqft
    Source: Smart MLS #24042374 Report a problem
    3/20/2014Listing removed$1,100,000$157/sqft
    Source: Keller Williams Realty #G635346 Report a problem
    5/14/2013Listed for sale$1,100,000$157/sqft
    Source: Keller Williams Realty #G635346 Report a problem
    5/11/2013Pending sale$1,100,000$157/sqft
    Source: Keller Williams Realty #G635346 Report a problem
    1/6/2013Price change$1,100,000-18.5%$157/sqft
    Source: Keller Williams Realty #G635346 Report a problem
    10/18/2012Price change$1,350,000+3.8%$193/sqft
    Source: Keller Williams Realty #G635346 Report a problem
    8/4/2012Listed for sale$1,300,000-27.8%$186/sqft
    Source: Borla & Associates LLC Real Estate #L140243 Report a problem
    4/6/2012Listing removed$1,800,000$257/sqft
    Source: Borla & Associates LLC Real Estate #L140243 Report a problem
    10/5/2011Listed for sale$1,800,000+800%$257/sqft
    Source: Borla & Associates LLC Real Estate #L140243 Report a problem
    10/30/1998Sold$200,000$29/sqft
    Source: Agent Provided Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$24,184 +10.5%$829,080
    2024$21,879 $829,080
    2023$21,879 +18.6%$829,080 +50.7%
    2022$18,447 $549,990
    2021$18,447 $549,990
    2020$18,447 $549,990
    2019$18,447 $549,990
    2018$18,447 +2.3%$549,990 +2.3%
    2017$18,029 +0.4%$537,530 +0.4%
    2016$17,951 +2.6%$535,220
    2015$17,502 +2.5%$535,220
    2014$17,079 +2.3%$535,220
    2013$16,699 +2.5%$535,220 -16.5%
    2012$16,295 $640,780
    2011$16,295 $640,780
    2010$16,295 +3.1%$640,780
    2009$15,808 $640,780
    2008$15,808 +35.8%$640,780 +88.6%
    2007$11,642 +3.6%$339,710 +0.8%
    2006$11,235 +16%$336,980 +14.8%
    2005$9,685 +151.3%$293,650 +129.5%
    2003$3,854 +20.4%$127,960 +10.2%
    1995$3,201 $116,130
    Find assessor info on the county website

    Neighborhood: 06098

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